Novel compounds, manufacturing process, use as pigments and cosmetic composition

ABSTRACT

The present invention relates to novel compounds corresponding to formula (I) below:  
                 
 
     The invention also relates to the process for manufacturing them, to their use as pigments and to a cosmetic composition comprising them.

[0001] The invention relates to a novel family of anthraquinonecompounds, to a process for manufacturing them and to their use aspigments, especially in cosmetics. The invention is also directedtowards cosmetic compositions containing them.

[0002] In the literature, the synthesis of colorants with ananthraquinone nucleus, in particular those substituted with amines, iswell known. One synthesis is especially described in patent FR 2 039381. Some of these colorants, such as those described in patent U.S.Pat. No. 5,486,629, are used for dyeing the hair.

[0003] These colorants are generally soluble in water or in apolar media(organic solvents and oils). They therefore cannot be used as insolublepigments in applications such as skin makeup, since a leachingphenomenon is observed.

[0004] Consequently, this family of colorants has very little potentialfor industrial development as pigments, although certain polymerizationprocesses, for instance the one described in patent U.S. Pat. No.4,279,662, or complex treatment processes such as the one described inpatent FR 2 060 730, have attempted to improve this persistent problem.

[0005] The Applicant has just discovered a novel family of anthraquinonecompounds containing urea bonding which may be used as pigments, inparticular in cosmetic compositions. These compounds, which are thesubject of the invention, are insoluble or very sparingly soluble inaqueous media, and also in organic solvents and oily media. They maythus solve the problem of leaching observed with the anthraquinonecolorants of the prior art, in these media, and in particular in oilymedia.

[0006] In addition, these novel compounds are very accessible since theyare prepared in a single step that is easy to carry out.

[0007] One subject of the present invention is thus novel anthraquinonecompounds of formula (I) below.

[0008] Another subject of the invention is a process for manufacturingthese novel compounds.

[0009] Yet another subject of the invention is the use of thesecompounds as pigments, especially in cosmetics.

[0010] A subject of the invention is also cosmetic compositionscontaining them.

[0011] Other subjects, characteristics, aspects and advantages of theinvention will emerge even more clearly on reading the description andthe various examples that follow.

[0012] According to the invention, the novel compounds correspond to thegeneral formula (I):

[0013] in which:

[0014] m and n, which may be identical or different, are between 1 and20;

[0015] X and Z each represent NH or O;

[0016] p is 0 or 1;

[0017] Y represents a carbon atom or a sulphur atom;

[0018] R₁, R′₁, R₅, R′₅, R₆, R′₆, R₇, R′₇, R₈, R′₈, R₉, R′₉, R₁₀ andR′₁₀, which may be identical or different, each represent a hydrogenatom, a halogen atom, a linear or branched, saturated or unsaturatedC₁₋₈ hydrocarbon-based group, a hydroxyl group,

[0019] R₂, R₃, R₄, R′₄ and R₁₁, which may be identical or different,each represent a hydrogen atom, a linear or branched, saturated orunsaturated, optionally hydroxylated, C₁₋₈ hydrocarbon-based group.

[0020] The hydrocarbon-based groups that are suitable in the presentinvention are linear or branched, saturated or unsaturated and containfrom 1 to 8 carbon atoms and preferably from 1 to 4 carbon atoms.

[0021] Hydrocarbon-based groups that may especially be mentioned includealkyl, alkenyl or alkynyl groups such as, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methylene, ethenylor ethynyl groups.

[0022] Halogen atoms that may especially be mentioned include chlorine,bromine, fluorine and iodine atoms, and preferably the chlorine atom.

[0023] The preferred compounds of the invention are those correspondingto formula (I) in which n=m, R′₁=R₁, R′₄=R₄, R′₅=R₅, R′₆=R₆, R′₇=R₇,R′₈=R₈, R′₉-R₉ and R′₁₀=R₁₀, Z=X and p=1, and the compounds that aremore particularly preferred correspond to the general formula (II)below:

[0024] in which:

[0025] n is from 1 to 12,

[0026] R₁ represents a hydrogen atom, a halogen atom, a linear orbranched, saturated or unsaturated C₁-C₈ hydrocarbon-based group, ahydroxyl group or a group —NR₂R₃, R₂, R₃ and R₄ each represent ahydrogen atom or a linear or branched, saturated or unsaturated C₁-C₈hydrocarbon-based group,

[0027] R₅ and R₆ each represent a hydrogen atom, a halogen atom, alinear or branched, saturated or unsaturated C₁-C₈ hydrocarbon-basedgroup or a hydroxyl group.

[0028] Examples of compounds of formula (I) or (II) above that mayespecially be mentioned include1,3-bis[3-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea and1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino)propyl]urea.

[0029] Another subject of the present invention is the process formanufacturing the compounds of formula (I) above.

[0030] This process consists in reacting together the anthraquinonederivatives of general formulae (III) and (IV) below:

[0031] in which A represents an activating group such as, especially, agroup derived from imidazole or a halogen atom, the other symbols havingthe same meaning as for formula (I);

[0032] in which R₁, R₄ to R₁₀, Z and n have the same meaning as forformula (I)

[0033] in the presence of a solvent and optionally a base, at atemperature from 0 to about 160° C., for about 30 minutes to about 20hours.

[0034] The solvents that are suitable in the present invention arepreferably dipolar aprotic solvents such as, for example,N,N-dimethylacetamide or N,N-dimethyl-formamide.

[0035] The bases that may be used are especially chosen from pyridine orits derivatives, triethylamine and diisopropylethylamine.

[0036] One preferred manufacturing process of the invention makes itpossible to obtain compounds of formula (I) above in which R′₁=R₁,R′₄=R₄, R′₅=R₅, R′₆=R₆, R′₇=R₇, R′₈=R₈, R′₉=R₉ and R′₁₀=R₁₀, n=m, Z=Xand p=1. It makes it possible, inter alia, to obtain the particularlypreferred compounds of formula (II) above.

[0037] The said process consists in reacting an anthraquinone derivativeof general formula (IV):

[0038] in which n, Z, R₁ and R₄ to R₁₀ are as defined above for formula(I), or one of its salts,

[0039] with phosgene or one of its derivatives or of its substitutes,for instance carbonyldiimidazole, at a temperature from 0 to about 160°C., for about 30 minutes to about 20 hours, in the presence of a solventas defined above, and optionally of a base as described above.

[0040] The invention also relates to the use as a pigment of at leastone compound of formula (I) or (II) as defined above, and preferably1,3-bis[3-(9,10-dioxo-9,10-di-hydroanthracen-1-ylamino)propyl]urea and1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea.

[0041] This novel family of pigments may be used in the food andcosmetics sectors and in paints, and preferably in cosmetics.

[0042] The cosmetic composition according to the invention comprises, ina cosmetically acceptable medium, at least one compound of formula (I)or (II) as defined above. This compound is especially contained in anamount of between 0.01% and 50% by weight and preferably between 0.1%and 25% by weight relative to the total weight of the composition.

[0043] The expression “cosmetically acceptable medium” means a mediumthat is compatible with all keratin materials such as the skin, thenails, the hair, the eyelashes, the eyebrows and the lips, and any otherarea of body or facial skin.

[0044] The said medium may comprise or be in the form of, for example, asuspension, a dispersion, a solution in solvent or aqueous-alcoholicmedium, optionally thickened, or even gelled; an oil-in-water,water-in-oil or multiple emulsion; a gel or a mousse; and emulsifiedgel; a dispersion of vesicles, especially a lipid dispersion; atwo-phase or multiphase lotion; a spray, a free, compact or cast powder;or an anhydrous paste.

[0045] A person skilled in the art may select the appropriatepresentation form, and also the method for preparing it, on the basis ofhis general knowledge, taking into account firstly the nature of theconstituents used, especially their solubility in the support, andsecondly the intended application for the composition.

[0046] When the composition is in aqueous form, especially in the formof a dispersion, an emulsion or an aqueous solution, it can comprise anaqueous phase which comprises water, a floral water and/or mineralwater.

[0047] The said aqueous phase may also comprise alcohols such as C₁-C₆monoalcohols and/or polyols such as glycerol, butylene glycol, isopreneglycol, propylene glycol or polyethylene glycol.

[0048] When the composition according to the invention is in the form ofan emulsion, it can optionally also comprise a surfactant, preferably inan amount from 0.01% to 30% by weight relative to the total weight ofthe composition. The composition according to the invention may alsocomprise at least one co-emulsifier which may be chosen fromoxyethylenated sorbitan monostearate, fatty alcohols such as stearylalcohol or cetyl alcohol, or fatty acid esters of polyols such asglyceryl stearate.

[0049] The composition according to the invention may also comprise oneor more thickeners in concentrations preferably ranging from 0 to 6% byweight relative to the total weight of the composition, chosen from:

[0050] polysaccharide biopolymers, for instance xanthan gum, carob gum,guar gum, alginates, modified celluloses, starch derivatives, celluloseether derivatives containing quaternary ammonium groups, and cationicpolysaccharides;

[0051] synthetic polymers, for instance poly(acrylic acid),polyvinylpyrrolidone, poly(vinyl alcohol) and acrylamide-based polymers;

[0052] magnesium aluminium silicate.

[0053] Depending on the intended application, the composition may alsocomprise a film-forming polymer. This is especially the case when it isdesired to prepare a composition of the type such as a nail varnish, amascara, an eyeliner or a haircare composition of the type such as alacquer. The polymers may be dissolved or dispersed in the cosmeticallyacceptable medium. In particular, the polymer may be present in the formof a solution in an organic solvent or in the form of an aqueousdispersion of film-forming polymer particles. The said polymer may bechosen from nitrocellulose, cellulose acetobutyrate, poly(vinylbutyrals), alkyd resins, polyesters, acrylic polymers, vinyl polymersand/or polyurethanes.

[0054] The composition may also comprise at least one plasticizer, whichmay be present in an amount ranging from 1% to 40% by weight relative tothe total weight of the composition.

[0055] The composition according to the invention may also comprise afatty phase, consisting especially of fatty substances that are liquidat 25° C., such as oils of animal, plant, mineral or synthetic origin;the fatty substances that are solid at 25° C., such as waxes of animal,plant, mineral or synthetic origin; pasty fatty substances; gums; ormixtures thereof.

[0056] The compositions according to the invention may thus comprisevolatile oils, which will evaporate on contact with the skin, but whosepresence in the cosmetic composition is useful since they make thecomposition easier to spread when it is applied to the skin. Thevolatile oils that are particularly suitable in the invention generallyhave, at 25° C., a saturating vapour pressure at least equal to 50 Pa(0.5 millibar).

[0057] Examples that may be mentioned include volatile silicone oils,such as:

[0058] cyclic volatile silicones containing from 3 to 8 and preferablyfrom 4 to 6 silicon atoms;

[0059] cyclocopolymers of the dimethylsiloxane/methylalkyl-siloxanetype;

[0060] linear volatile silicones containing from 2 to 9 silicon atoms.

[0061] Mention may also be made of volatile hydrocarbon-based oils suchas isoparaffins and especially isododecane and fluoro oils.

[0062] Non-volatile oils can also be used, among which mention may bemade of:

[0063] poly(C₁-C₂₀)alkylsiloxanes and especially those containingtrimethylsilyl end groups, among which mention may be made of linearpolydimethylsiloxanes and alkylmethylpolysiloxanes such ascetyldimethicone (CTFA name);

[0064] silicones modified with aliphatic and/or aromatic groups, whichmay be fluorinated, or with functional groups such as hydroxyl, thioland/or amine groups;

[0065] phenylsilicone oils, especially those of formula:

[0066] in which R represents a C₁-C₃₀ alkyl group, an aryl group or anaralkyl group, q is an integer between 0 and 100, and r is an integerbetween 0 and 100, with the proviso that the sum is between 1 and 100;

[0067] oils of animal, plant or mineral origin, and especially animal orplant oils formed from fatty acid esters of polyols, in particularliquid triglycerides, for example sunflower oil, corn oil, soybean oil,marrow oil, grapeseed oil, sesame oil, hazelnut oil, apricot oil, almondoil or avocado oil; fish oils, glyceryl tricaprocaprylate, or plant oranimal oils of formula R_(a)COOR_(b) in which R_(a) represents a fattyacid residue containing from 7 to 19 carbon atoms and R_(b) represents abranched hydrocarbon-based chain containing from 3 to 20 carbon atoms,for example purcellin oil; liquid paraffin, liquid petroleum jelly,perhydrosqualene, wheatgerm oil, beauty-leaf oil, sesame oil, macadamiaoil, grapeseed oil, rapeseed oil, coconut oil, groundnut oil, palm oil,castor oil, jojoba oil, olive oil or cereal germ oil; fatty acid esters;alcohols; acetylglycerides; octanoates, decanoates or ricinoleates ofalcohols or of polyalcohols; fatty acid triglyercides; glycerides;

[0068] fluoro oils and perfluoro oils.

[0069] The composition according to the invention may also compriseother fatty substances that may be chosen by a person skilled in the arton the basis of his general knowledge, so as to give the finalcomposition the desired properties, for example in terms of consistencyand/or texture. These additional fatty substances may be waxes, gumsand/or pasty fatty substances of animal, plant, mineral or syntheticorigin, and also mixtures thereof. Mention may be made especially ofsilicone gums; waxes of animal, plant, mineral or synthetic origin, suchas microcrystalline waxes, paraffin, petrolatum, petroleum jelly,ozokerite or montan wax; beeswax, lanolin and its derivatives;candelilla wax, ouricury wax, carnauba wax, Japan wax, cocoa butter,cork fibre wax or sugarcane wax; hydrogenated oils, ozokerites, fattyesters and glycerides; polyethylene waxes and the waxes obtained byFischer-Tropsch synthesis; lanolins; silicone waxes; fluoro waxes;polyolefins.

[0070] The composition may also contain nacres and/or fillers, and alsoother pigments that are well known in the art.

[0071] The nacres may be present in the composition in a proportion offrom 0 to 20% by weight and preferably from 8% to 15% by weight, and maybe chosen from natural mother-of-pearl, mica coated with titanium oxide,with iron oxide, with natural pigment or with bismuth oxychloride, andalso coloured titanium mica.

[0072] The fillers, which may be present in a proportion of from 0 to30% by weight and preferably from 5% to 15%, in the composition, may bemineral or synthetic, and lamellar or non-lamellar. Mention may be madeof talc, mica, silica, kaolin, nylon powder, polyethylene powder,Teflon, starch, boron nitride, polymer microspheres such as Expancel®(Nobel Industrie), Polytrap® (Dow Corning) and silicone resin microbeads(for example Tospearls® from Toshiba), precipitated calcium carbonate,magnesium carbonate, magnesium hydrocarbonate and metal soaps derivedfrom organic carboxylic acids containing from 8 to 22 carbon atoms.

[0073] The composition may also comprise a water-soluble or liposolublecolorant, especially a natural organic colorant such as cochinealcarmine, and/or a synthetic colorant such as halo acid dyes, azo dyes oranthraquinone dyes. Mention may also be made of mineral colorants suchas copper sulphate.

[0074] The composition may also comprise any additive usually used incosmetics, such as fragrances, essential oils, preserving agents,lipophilic or hydrophilic cosmetic active agents, moisturizers,vitamins, essential fatty acids, sphingolipids, self-tanning agents suchas dihydroxyacetone (DHA), sunscreens, antifoams, sequestering agents,antioxidants and dispersants. Needless to say, a person skilled in theart will take care to select the optional additional compound(s)mentioned above, such that the advantageous properties intrinsicallyassociated with the dye composition according to the invention are not,or are not substantially, adversely affected by the envisagedaddition(s)

[0075] The cosmetic compositions according to the invention may be:

[0076] in the form of a makeup product for facial or body skin or thelips or keratin fibres (nails, eyelashes, eyebrows or hair), such as afoundation, a tinted cream, a face powder, an eye shadow, a free orcompact powder, a concealer stick, a cover stick, an eyeliner, amascara, a lipstick, a nail varnish or a hair makeup composition;

[0077] in the form of a skincare product for the face or the bodyincluding the scalp, such as a facial care composition (day product,night product, anti-wrinkle product, moisturizing product, etc.); amatt-effect composition for the face;

[0078] in the form of an antisun composition or an artificial tanning(self-tanning) composition; or

[0079] in the form of a hair composition, and especially a styling creamor gel, a dye composition or oxidation dye composition, optionally inthe form of a colouring shampoo.

[0080] The examples that follow are intended to illustrate the inventionand should not be considered in any way as limiting the invention.

EXAMPLE 1

[0081] Preparation of1,3-bis[3-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea(formula (II) with R₁, R₄, R₅, R₆=H and n=3)

[0082] 5 g (17.84 mmol) of 1-[(3-aminopropyl)amino]-9,10-anthracenedionewere partially dissolved at room temperature in 200 ml ofdimethylformamide in a 250 ml three-necked flask, under a nitrogenatmosphere. 1.5 g (0.55 eq.) of carbonyldiimidazole were then added.

[0083] The mixture was then stirred for 1 hour at room temperature andthen heated to 40° C. for 5 hours. After filtration, washing with waterand acetone and then drying under vacuum at 50° C., 4.5 g of a dark redpowder were obtained (final yield of 90%).

[0084] The characteristics of the final product are as follows:

[0085] melting point above 260° C. (measured on a Kofler block),

[0086] mass spectrum (SSQ710, CI-DI): m/z=587,

[0087] elemental analysis (C₃₅H₃₀N₄O₅, MW=586.653): C H N O % calculated71.66 5.15 9.55 13.64 % found 71.03 5.11 9.89 14.19

EXAMPLE 2

[0088] Preparation of1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea(formula (II) with R₄, R₅ and R₆=H, R₁=NHCH₃ and n=3)

[0089] 5 g (16.27 mmol) of 1-[(3-aminopropyl)amino]-9,10-anthracenedionewere partially dissolved at room temperature in 200 ml ofdimethylformamide in a 250 ml three-necked flask under a nitrogenatmosphere. 1.45 g (0.5 eq) of carbonyldiimidazole were then added.

[0090] The mixture was first stirred for 1 hour at room temperature andthen heated at 40° C. for 6 hours. After filtration, washing with waterand acetone and then drying under vacuum at 50° C., 3.9 g of apurple-blue powder were obtained (final yield of 73%).

[0091] The characteristics of the final product are as follows:

[0092] melting point above 260° C. (measured on a Kofler block),

[0093] mass spectrum (SSQ710, EI-DEP): m/z=644,

[0094] elemental analysis (C₃₇H₃₆N₆O₅, MW=644.7280): C H N O %calculated 68.93 5.63 13.03 12.41 % found 67.91 5.56 13.03 12.94

[0095] Formulation Example No. 1 A tinted cream of oil-in-water emulsiontype is prepared from the following ingredients: Parleam oil 22 gStearic acid 1.5 g Polysorbate 60⁽¹⁾ (sold under the trade 0.9 g nameTween ® 60 by the company ICI) Cetyl alcohol 0.5 g Glycerylmonostearate/PEG 100 stearate 2.1 g mixture Triethanolamine 0.75 gCompound of Example 1 5 g Propylene glycol 3 gCyclopentadimethylsiloxane 3 g Carbopol 981 0.15 g Xanthan gum 0.2 gWater qs 100 g Formulation Example No. 2 An eye shadow is prepared fromthe following ingredients: Talc 38 g Mica 20 g Bismuth oxychloride 8 gZinc stearate 3 g Nylon powder 20 g Compound of Example 2 5 g Waterqs 100 g A stable blue eye shadow that has good cosmetic properties isobtained. Formulation Example No. 3 A lipstick is prepared from thefollowing ingredients: Polyethylene wax 15 g Compound of Example 1 10 gParleam oil qs 100 g A lipstick with good cosmetic properties isobtained.

1. Compounds corresponding to the general formula (I):

in which: m and n, which may be identical or different, are between 1and 20; X and Z each represent NH or O; p is 0 or 1; Y represents acarbon atom or a sulphur atom; R₁, R′₁, R₅, R′₅, R₆, R′₆, R₇, R′₇, R₈,R′₈, R₉, R′₉, R₁₀ and R′₁₀, which may be identical or different, eachrepresent a hydrogen atom, a halogen atom, a linear or branched,saturated or unsaturated C₁₋₈ hydrocarbon-based group, a hydroxyl group,

R₂, R₃, R₄, R′₄ and R₁₁, which may be identical or different, eachrepresent a hydrogen atom, a linear or branched, saturated orunsaturated, optionally hydroxylated, C₁₋₈ hydrocarbon-based group. 2.Compounds corresponding to the general formula (II):

in which: n is from 1 to 12, R₁ represents a hydrogen atom, a halogenatom, a linear or branched, saturated or unsaturated C₁-C₈hydrocarbon-based group, a hydroxyl group or a group —NR₂R₃, R₂, R₃ andR₄ each represent a hydrogen atom or a linear or branched, saturated orunsaturated C₁-C₈ hydrocarbon-based group, R₅ and R₆ each represent ahydrogen atom, a halogen atom, a linear or branched, saturated orunsaturated C₁-C₈ hydrocarbon-based group or a hydroxyl group. 3.Compounds according to claim 1 or 2, characterized in that they arechosen from 1,3-bis[3-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea and1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino)propyl] urea.
 4. Process for manufacturing the compounds according toclaim 1, characterized in that the anthraquinone derivatives of generalformulae (III) and (IV):

in which: A represents an activating group such as a group derived fromimidazole or a halogen atom, m is between 1 and 20; X represents NH orO; p is 0 or 1; Y represents a carbon atom or a sulphur atom; R′₁, R′₅,R′₆, R′₇, R′₈, R′₉ and R′₁₀, which may be identical or different, eachrepresent a hydrogen atom, a halogen atom, a linear or branched,saturated or unsaturated C₁₋₈ hydrocarbon-based group, a hydroxyl group,

R₂, R₃, R′₄ and R₁₁, which may be identical or different, each representa hydrogen atom, a linear or branched, saturated or unsaturated,optionally hydroxylated C₁₋₈ hydrocarbon-based group; and

in which: n is between 1 and 20; Z represents NH or O; R₁, R₅, R₆, R₇,R₈, R₉ and R₁₀, which may be identical or different, each represent ahydrogen atom, a halogen atom, a linear or branched, saturated orunsaturated C₁₋₈ hydrocarbon-based group, a hydroxyl group,

R₂, R₃, R₄ and R₁₁, which may be identical or different, each representa hydrogen atom, a linear or branched, saturated or unsaturated,optionally hydroxylated C₁₋₈ hydrocarbon-based group; are reactedtogether in the presence of a solvent and optionally of a base, at atemperature from 0 to about 160° C. for about 30 minutes to about 20hours.
 5. Manufacturing process, characterized in that it consists inreacting an anthraquinone derivative of general formula (IV):

in which: n is between 1 and 20; Z represents NH or O; R₁, R₅, R₆, R₇,R₈, R₉ and R₁₀, which may be identical or different, each represent ahydrogen atom, a halogen atom, a linear or branched, saturated orunsaturated C₁₋₈ hydrocarbon-based group, a hydroxyl group,

R₂, R₃, R₄ and R₁₁, which may be identical or different, each representa hydrogen atom, a linear or branched, saturated or unsaturated,optionally hydroxylated C₁₋₈ hydrocarbon-based group; with phosgene orone of its derivatives or of its substitutes, for instancecarbonyldiimidazole, at a temperature from 0 to about 160° C. for about30 minutes to about 20 hours, in the presence of a solvent andoptionally a base.
 6. Process according to claim 4 or 5, characterizedin that the solvent is a dipolar aprotic solvent.
 7. Process accordingto any one of claims 4 to 6, characterized in that the solvent isN,N-dimethyl-acetamide or N,N-dimethylformamide.
 8. Process according toany one of claims 4 to 7, characterized in that the base is chosen frompyridine or its derivatives, triethylamine and diisopropyl-ethylamine.9. Use, as a pigment, of at least one compound according to claim 1 or2.
 10. Use according to claim 9, characterized in that the compounds arechosen from1,3-bis[3-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea and1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino)propyl]urea.11. Use, as a pigment, of at least one compound according to claim 1, 2or 3, in a cosmetic composition.
 12. Cosmetic composition, characterizedin that it comprises, in a cosmetically acceptable medium, at least onecompound according to claim 1 or
 2. 13. Cosmetic composition accordingto claim 12, characterized in that the compound is chosen from1,3-bis[3-(9,10-dioxo-9,10-dihydroanthracen-1-ylamino)-propyl]urea and1,3-bis[3-(4-methylamino-9,10-dioxo-9,10-dihydroanthracen-1-ylamino)propyl]urea.14. Cosmetic composition according to claim 12 or 13, characterized inthat the said compound is contained in an amount ranging from 0.01% to50% by weight.
 15. Cosmetic composition according to claim 14,characterized in that the said compound is contained in an amountranging from 0.1% to 25% by weight.
 16. Cosmetic composition accordingto any one of claims 12 to 15, characterized in that the cosmeticallyacceptable medium comprises or is in the form of a suspension, adispersion, a solution in solvent or aqueous-alcoholic medium,optionally thickened, or even gelled; an oil-in-water, water-in-oil ormultiple emulsion; a gel or a mousse; an emulsified gel; a dispersion ofvesicles; a two-phase or multiphase lotion; a spray; a free, compact orcast powder; or an anhydrous paste.
 17. Cosmetic composition accordingto any one of claims 12 to 16, characterized in that it is in the formof a makeup product for facial or body skin or the lips or keratinfibres; a skincare product for the face or the body; an antisuncomposition or artificial tanning composition; or a haircarecomposition.